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Showing NP-Card for Quercetin 3-arabinoside (NP0336728)

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Record Information
Version2.0
Created at2024-09-11 07:35:03 UTC
Updated at2024-09-11 07:35:03 UTC
NP-MRD IDNP0336728
Secondary Accession NumbersNone
Natural Product Identification
Common NameQuercetin 3-arabinoside
DescriptionQuercetin 3-arabinoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Quercetin 3-arabinoside was first documented in 2008 (PMID: 18596658). Based on a literature review a small amount of articles have been published on Quercetin 3-arabinoside (PMID: 33126563) (PMID: 19085814).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336728 (Quercetin 3-arabinoside)


  Mrv2104 05262310072D          

 31 34  0  0  0  0            999 V2000
   -1.7862   -1.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -1.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    3.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    1.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    2.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260   -1.2703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8411   -1.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260   -2.6051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1107   -2.3502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1107   -1.5252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0711   -0.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -2.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -3.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -4.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 27 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 30 31  1  0  0  0  0
M  END
Download

3D MOL for NP0336728 (Quercetin 3-arabinoside)

Download
3D SDF for NP0336728 (Quercetin 3-arabinoside)

  Mrv2104 05262310072D          

 31 34  0  0  0  0            999 V2000
   -1.7862   -1.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -1.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -0.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    3.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    1.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    2.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260   -1.2703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8411   -1.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260   -2.6051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1107   -2.3502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1107   -1.5252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0711   -0.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -2.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -3.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -4.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 27 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20+/s2

> <INCHI_KEY>
BDCDNTVZSILEOY-ITOUDFAFNA-N

> <FORMULA>
C20H18O11

> <MOLECULAR_WEIGHT>
434.353

> <EXACT_MASS>
434.0849114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.04760878313979

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <JCHEM_LOGP>
0.4854996460000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872523610896667

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372405621031869

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981152416465515

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
103.31299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336728 (Quercetin 3-arabinoside)
Download
PDB for NP0336728 (Quercetin 3-arabinoside)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0      -3.334  -2.447   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.334  -0.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.669  -0.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.669   1.403   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.334   2.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.002   1.403   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.002  -0.137   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667  -0.907   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.667  -2.447   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -6.001   2.173   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.667  -0.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.667   1.403   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.667   2.173   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.334   6.023   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.334   4.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.999   3.713   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.999   2.173   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.334   1.403   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.669   2.173   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.669   3.713   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.001   4.483   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.475  -2.371   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.570  -3.617   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.475  -4.863   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.940  -4.387   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.940  -2.847   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.999  -0.907   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.186  -1.942   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.186  -5.292   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.999  -6.328   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.030  -7.472   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11    8   27   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13    6   12                                                       
CONECT   14   15                                                            
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
CONECT   22   23   26   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   22   28                                                  
CONECT   27   11   22                                                       
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0336728 (Quercetin 3-arabinoside)
Download
SMILES for NP0336728 (Quercetin 3-arabinoside)
OC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O
Download
INCHI for NP0336728 (Quercetin 3-arabinoside)
InChI=1/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20+/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H18O11
Average Mass434.3530 Da
Monoisotopic Mass434.08491 Da
IUPAC Name3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Name3-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O
InChI Identifier
InChI=1/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20+/s2
InChI KeyBDCDNTVZSILEOY-ITOUDFAFNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid-3-O-glycosides  
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Pentose monosaccharide
    • 

  • Catechol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Monosaccharide
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Tetrahydrofuran
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Primary alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.49ChemAxon
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.31 m³·mol⁻¹ChemAxon
Polarizability41.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Amaral JS, Valentao P, Andrade PB, Martins RC, Seabra RM: Do cultivar, geographical location and crop season influence phenolic profile of walnut leaves? Molecules. 2008 Jun 12;13(6):1321-32. doi: 10.3390/molecules13061321. [PubMed:18596658  ] 
  2. Zielinska D, Turemko M: Electroactive Phenolic Contributors and Antioxidant Capacity of Flesh and Peel of 11 Apple Cultivars Measured by Cyclic Voltammetry and HPLC-DAD-MS/MS. Antioxidants (Basel). 2020 Oct 28;9(11):1054. doi: 10.3390/antiox9111054. [PubMed:33126563  ] 
  3. McIntyre KL, Harris CS, Saleem A, Beaulieu LP, Ta CA, Haddad PS, Arnason JT: Seasonal phytochemical variation of anti-glycation principles in lowbush blueberry (Vaccinium angustifolium). Planta Med. 2009 Feb;75(3):286-92. doi: 10.1055/s-0028-1088394. Epub 2008 Dec 15. [PubMed:19085814  ]